Lithium borohydride → HCID 86689149, compound

HRID 1752466Notes

Reaction equation

HRID 1752466 reaction equation
C([O:3][C:4](=O)[C:5]([F:27])([F:26])[C@@:6]([C:18]1[C:23]([F:24])=[CH:22][CH:21]=[C:20]([Br:25])[N:19]=1)([NH:11][S@:12]([C:14]([CH3:17])([CH3:16])[CH3:15])=[O:13])[CH2:7][CH2:8][O:9][CH3:10])C.[BH4-].[Li+]>C1COCC1.C(OCC)(=O)C>[Br:25][C:20]1[N:19]=[C:18]([C@:6]([NH:11][S@:12]([C:14]([CH3:16])([CH3:15])[CH3:17])=[O:13])([CH2:7][CH2:8][O:9][CH3:10])[C:5]([F:27])([F:26])[CH2:4][OH:3])[C:23]([F:24])=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 86689150HCID 86689150, compound

Product 1

HCID 86689149HCID 86689149, compoundYield 68.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-3-(6-bromo-3-fluoro-pyridin-2-yl)-2,2-difluoro-5-methoxy-3-((S)-2-methyl-propane-2-sulfinylamino)-pentanoic acid ethyl ester (2.4 g, 4.90 mmol) in THF (38 ml) was added lithiumborohydride (214 mg, 9.81 mmol) in 2 portions. The slightly exothermic reaction was stirred for 6 hours at room temperature. Crushed ice was added carefully and the reaction mixture was diluted with ethyl acetate. The organic phase was washed with water and brine, dried over sodium sulfate, filtered and evaporated. The crude yellowish resin (2.05 g) was chromatographed over silica gel (Redisep column 40 g, cyclohexane/ethyl acetate 4:6) to give the title compound as a colourless resin. 1.50 g (68.4% yield).

Workup

  1. customThe slightly exothermic reaction
  2. additionCrushed ice was added carefully
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude yellowish resin (2.05 g) was chromatographed over silica gel (Redisep column 40 g, cyclohexane/ethyl acetate 4:6)

Sources & evidence

ORD record
ord-ac6e16acd6df4c51beb2644052c9e61d
Source dataset
uspto-grants-2015_10
Patent number
US09163011B2

Reaction notes

Loading…